Further Studies on the Side Reactions Associated with Use of Nπ- Benzyloxymethylhistidine

Title: Further Studies on the Side Reactions Associated with Use of Nπ- Benzyloxymethylhistidine

Volume: 12 Issue: 6

Author(s): Kumiko Yoshizawa-Kumagaye, Takehiro Ishizu, Shuji Isaka, Masaji Tamura, Rumi Okihara, Yuji Nishiuchi and Terutoshi Kimura

Affiliation:

Keywords: benzyloxymethyl (bom), dihydroqunazolin, formaldehyde, hf, n-methylanthranyl (nma), tetrahydro carboline

Abstract: The use of Nα-tert.-butyloxycarbonyl-Nπ-benzyloxymethylhistidine [Boc-His(Bom)] in peptide synthesis results in a serious level of side products arising from the generation of formaldehyde during the HF cleavage reaction. In particular, when treating a His(Bom)-containing peptide having Cys at the N-terminus by HF, this leads to almost complete conversion of the Cys-peptide to thiazolidyl (Thz)-peptide unless precautions are taken. Also, the reaction of formaldehyde with the N-terminal Trp and the N-methylanthranyl (Nma) group was found to produce tetrahydro-β- carboline and dihydroquinazolin derivatives, respectively, upon isolation from HF mixtures. The addition of cysteine as a scavenger in HF proved to be effective for suppressing modification arising from the generation of formaldehyde.

Cite this article as:

Yoshizawa-Kumagaye Kumiko, Ishizu Takehiro, Isaka Shuji, Tamura Masaji, Okihara Rumi, Nishiuchi Yuji and Kimura Terutoshi, Further Studies on the Side Reactions Associated with Use of Nπ- Benzyloxymethylhistidine, Protein & Peptide Letters 2005; 12 (6) . https://dx.doi.org/10.2174/0929866054395789

DOI https://dx.doi.org/10.2174/0929866054395789	Print ISSN 0929-8665
Publisher Name Bentham Science Publisher	Online ISSN 1875-5305